From honeymoon suites in old windmills to dramatic cliffside villas, several hotels in the Caribbean offer a glimpse into island history as well as a place to rest your head. These charming spots are often smaller, more intimate, and more sensitive to their settings. And they excel in gracious Caribbean hospitality.

BERMUDA’S WATERLOO HOUSE

Built in 1815 as a private manor and set on four terraced acres of gardens, Waterloo House harks back to a Bermuda of long ago. Chintz meets Relais & Châteaux in this small hotel within walking distance to historic sites, shopping, and restaurants of Hamilton, the island’s capital. But you might just want to eat here, either a gourmet dinner in the Wellington Room or a more casual meal harborside at the Poinciana Terrace. Rates: $340 to $780. Con-tact: 800-468-4100, www.waterloohouse.com.

Courtesy of Guana Island

B.V.I.’S, GUANA ISLAND

Is it a nature preserve? A private island resort? A little of both, actually. Once a sugarcane plantation owned by Quakers, the unpretentious 850-acre resort is a haven for such rare bird species as the masked booby and the bridled quail dove. Guests find a haven in the under-statedly elegant rooms, housed in stone buildings. With 7 stunning beaches on the island and a maximum of just 30 guests, you can bet you’ll find a strand to yourself. Naturalists visit from as far away as Asia to study the avian population (the island closes in September and October for scientific research), but if you’re not into birding, there’s windsurfing, croquet, and tennis to break up your beach days. Rates: $595 to $1,850. Contact: 914-967-6050, www.guana.com.

Just over the Queen Emma Bridge from Willemstad’s colorful waterfront sits Hotel Kurá Hulanda, an 80-room boutique hotel, a magnificent restoration project by Dutch businessman and hotelier Jacob Dekker. Reclaiming eight blocks of 18th- and 19th-century Dutch colonial buildings and adding others in the same architectural style, Dekker has created a historic hotel of the utmost contemporary chic. Indonesian furniture fills the guest rooms, reflecting Curaçao’s past as a major trading center. Located just a block from the port where merchant vessels once docked (now it’s cruise ships), Kurá Hulanda has revitalized the once-neglected Otrabanda side of this capital city. Even if you don’t plan to stay at the hotel, make time to see the museum on site (open daily 10 a.m. to 5 p.m.). It displays art and artifacts of Curaçao’s predominant cultures that Dekker personally collected. Rates: $200 to $1,000. Contact: 877-264-3106, www.kurahulanda.com.

Courtesy of The Caves

JAMAICA’S THE CAVES

The Caves is all about fine Jamaican style. Reggae wafts in on the breeze, mingling with the sounds of the Caribbean Sea that swirl through the caves and around the volcanically formed cliffs where the hotel’s ten villas are perched. Nestled on the southern end of Negril next to the historic lighthouse, there’s no beach, but you won’t miss it once you choose your own nook for two among the private terraces that dot the two-acre property. Coral stairways lead directly into the calm waters, so you can easily take a dip. Decorated in bright island batiks and built of wood and stone with thatched roofs, each cottage has its own distinct style and name. (One Drop is one of the original A-frame units.) In the restaurant, you’ll find sophisticated takes on Caribbean cuisine, which you can savor by candlelight in a cave dining room for two. Rates: $445 to $925, includes all food and beverages. Contact: 800-OUTPOST, www.islandoutpost.com/Caves.

ST. BARTS’ VILLAS

Slideshow: Caribbean way of life
St. Barts is not about big hotels, but it is about big names: Celebs, that is, the kind who grace the cover of People magazine. Where do they stay on the island? In one of many private villas available for rent. It’s the way to go on this tiny island that has been spared mega-resort development, thanks to local restrictions. Book a modest one-bedroom cottage and cook for yourself (grocery stores are easy to find) or live large in a sprawling mansion and hire a chef. Find beachfront spots in St. Jean, Lorient, Cul de Sac, and Flamands, but many of the villas are set on the hillside, so you’ll want to rent a car. No matter where you end up, you’ll be living like the locals, who blend French chic with American casual style. Rates: approximately $2,000 to $45,000 per week. See www.stbarth.com or www.st-barths.com for a list of rental villas.

NEVIS’ MONTPELIER PLANTATION INN

Admiral Horatio Nelson married Frances Nisbet at this historic property in 1787, when it was a working sugar plantation. Today, just a bit of the sugar used in Montpelier’s kitchens is harvested on the 30-acre estate. Perched 750 feet above the sea, the 17 newly restored guest rooms have views of the ocean and lush countryside.

Courtesy of Kurá Hulanda

The Botanical Gardens of Nevis, on the grounds of the original plantation, are just a five-minute walk from the inn, or you can play a round of golf among the ruins at the nearby Robert Trent Jones II course at the Four Seasons Resort Nevis. To roam farther afield, take a guided mountain-biking tour of the island. Routes follow the island’s old plantation roads and trails. Rates: $260 to $650 per night, including full English breakfast and afternoon tea. If you ship your luggage ahead via FedEx, Montpelier will unpack, press, and put away your clothes for you. Contact: 869-469-3462, www.montpeliernevis.com.

Courtesy of Caneel Bay

ST. JOHN’S CANEEL BAY

The late Laurance Rockefeller had the vision to preserve this jewel of the USVI in the mid-1950s. He created Caneel Bay on seven secluded white sand beaches (two are designated “quiet;” kids are more than welcome at the other five), while preserving 5,000 acres of St. John as the Virgin Islands National Park. The minute you enter the manicured grounds of Caneel Bay, it becomes clear that this is a luxurious place—and utterly without glitz.

The sense of escape is complete: You’d never believe that there are 166 guest rooms on the 170-acre property, which seems even bigger because it’s tucked within the park. Many rooms open right onto charming white-sand coves, where the warm clear water makes for great snorkeling and swimming. Kids—heck, adults, too—love to explore the sugar-mill ruins on the property. This is a casual place, and the only dressing up you’ll have to do is for dinner at Turtle Bay Estate House. It’s a small price to pay for complete relaxation all day long. Rates: $325 to $1,150. Contact: 340-776-6111, www.caneelbay.com.

ST. KITTS’ RAWLINS PLANTATION

Located on the slopes of Mount Liamuiga, Rawlins isn’t your typical beachfront Caribbean resort. Just ten rooms grace this former sugar plantation, now known for the gourmet cuisine that chef and owner Claire Rawson prepares. The old plantation buildings have been converted into guest cottages, set among 12 acres of landscaped grounds and gardens; the honeymoon suite occupies an old windmill. Laze in a hammock strung between palm trees and watch the acres of sugarcane sway in the breeze, or just gaze out toward the Dutch and French Antilles not far away. There’s a spring-fed swimming pool; grass tennis court; and mango, papaya, avocado, and breadfruit trees to stroll around, but no minibars, TVs, telephones, or air-conditioning. It’s as authentic as it gets. Rates: $240 to $470, includes meals and laundry service. Contact: 869-465-6221,
www.rawlinsplantation.com.

Courtesy of The Windmills Planta

TURKS AND CAICOS’ THE WINDMILLS PLANTATION

This eight-room inn on a stretch of Salt Cay’s white beach was built in 1990 to look like an old salt-plantation house—it might be relatively new, but the vibe here is that of a sleepy Caribbean of long ago. Windmills in the old salinas and stone ruins around the island recall its salt-producing past. Now known for its great wreck-diving, the tiny island also has a two-mile-long reef just off the beach that’s perfect for snorkeling. If you tire of making footprints on the beach, there’s fishing, nature trails, and a saltwater pool to enjoy. Rates: $495 to $595. Contact: 800-225-4255, www.windmillsplantation.com.

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